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Guilherme Mazui

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What is the Difference Between Enantiotopic and Diastereotopic?

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The difference between enantiotopic and diastereotopic lies in the products formed when two protons are replaced with a different group (X). The relationships between protons are important for understanding their behavior in NMR spectroscopy and other chemical properties.

  • Enantiotopic Protons: If replacing two protons with a different group (X) results in a pair of enantiomers, the protons are called enantiotopic. Enantiotopic protons have different environments and always result in enantiomers upon replacement with a different atom.
  • Diastereotopic Protons: If replacing two protons with a different group (X) results in a pair of diastereomers, the protons are called diastereotopic. Diastereotopic protons have different environments and result in diastereomers upon replacement with a different atom. In general, diastereotopic protons occur when there is a chirality center already present in the molecule.

In summary, the main difference between enantiotopic and diastereotopic protons is the type of stereoisomers formed when the protons are replaced with a different atom. Enantiotopic protons result in enantiomers, while diastereotopic protons result in diastereomers.

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  • What is the Difference Between Enantiotopic and Diastereotopic?
  • Comparative Table: Enantiotopic vs Diastereotopic

    • Comparative Table: Enantiotopic vs Diastereotopic

    Here is a table comparing the differences between enantiotopic and diastereotopic hydrogens:

    Property Enantiotopic Diastereotopic
    Definition Enantiotopic refers to the ability to form a chiral center, where replacement of each hydrogen with deuterium results in enantiomers. Diastereotopic refers to the replacement of each hydrogen with deuterium results in diastereomers, which have different chemical properties.
    Stereochemical Relationship Enantiotopic hydrogens form enantiomers, which are mirror images of each other and cannot be superimposed. Diastereotopic hydrogens form diastereomers, which are not mirror images of each other and have different chemical properties.
    NMR Spectroscopy Enantiotopic hydrogens typically produce one signal in a 1H NMR spectrum, as they are chemically equivalent. Diastereotopic hydrogens produce multiple signals in a 1H NMR spectrum, as they are chemically non-equivalent.
    Example In butane, the hydrogen atoms attached to the second and third carbon atoms are enantiotopic. In bromochloromethane (C2H4BrCl), the hydrogens are diastereotopic.
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    Guilherme Mazui

    Guilherme Mazui is graduated in journalism from the Federal University of Minas Gerais (UFMG) and a master's degree in Communication from the University of São Paulo (USP). In addition, he has experience in advertising writing and has worked as a content editor in several companies.